The To Do List is loaded with people you love: Aubrey Plaza, Donald Glover, Alia Shawkat, Rachel Bilson, Scott Porter, Connie Britton, and Adam Pally, and it does one hell of a number on the losing-your-virginity subgenre, brilliantly subverting the conservative conventions that still generally provide the backbone to even the raunchiest of teen comedies. There are times in The To Do List when Aubrey Plaza takes it further than Jason Biggs’ pastry fucking, and it is refreshing, and amazing to see the gender-flipping at play, to see the women take the lead in a comedy like this, and to see Plaza transform talking with a mouth full of cum into an empowering gag.

There is, however, almost no emotional core to The To Do List, and maybe that’s the point to what is an anti-John Hughes film. It takes that American Pie formula about scrubbing one’s virginity in the summer before college and flips it. This is not about Jim Levenstein finding the sweet girl with the kinky predilections, or even Preston Meyers finding his soul mate. It’s about a woman who just wants to fuck, to climb the tower of sexual experiences. She has no interest in forging an emotional connection, even at the risk of hurting the men she uses to cross off her To Do List.

It’s kind of amazing.

Unfortunately, it’s also not that funny, and while it is novel to eschew the emotional underpinning that makes a movie like Can’t Hardly Wait and Clueless so successful, it also fails to really connect with the audience, which may appreciate the daringness of The To Do List even without particularly enjoying it. There is, however, a certain second-rate Wet Hot American Summer humor that occasionally works, but too often, The To Do List feels like a series sexually charged sketches that never quite cohere.

Set in 1993 to (poorly) take advantage of the gags in music and fashion inherent in the early 90s style, Aubrey Plaza is Brandy Klark, your prototypical type A high-school valedictorian, played by Plaza a little too straight, as though she’s somewhere on the spectrum. She decides, after being laughed at during her valedictorian speech for being a virgin, to rid herself of that pesky nuisance before she goes to college. She turns the challenge into a To Do List of sexual experiences: Hand job, masturbation, cunnilingus, blow job, etc. that she checks off with a kind of OCD indifference. Her ultimate goal, however, is to conquer Rusty Waters (Scott Porter), a long-haired, shirtless guitar Golden God, who attacks Def Leppard songs with all the douchiness of John Mayer.

To get there, however, she has to run through her list, which provides the canvas upon which writer/director Maggie Carey paints the gross-out gags. In between each step on the bone ladder, she seeks the advice and counsel of her two best friends (Alia Shawkat and Sarah Steele), her slutty sister (Rachel Bilson), and her mom (Connie Britton), who provides intimate sexual advice with that wonderful Connie Britton matter-of-factness. (“Here’s some lube. You put this in your vagina.”) Clark Gregg plays her father, whose conservative boundaries both Brandy and her sister push up against, while Johnny Simmons basically plays Ethan Embry in Can’t Hardly Wait. [It should also be noted that, though most of these characters are playing high school students, no one is under the age of 25 (and some, like Plaza, are pushing 30), but like Wet Hot American Summer, that’s also part of the joke.]

Unfortunately, with the exception of Bill Hader’s dazed-and-confused stoner lifeguard who can’t swim, who provides a fleeting moment or two of pathos, it’s damn near impossible to connect with any of the characters. The women play sounding boards, while the men basically exist for the same reason that women exist in most of these other films: As sexual tools. That’s brazen, and interesting, and if The To Do List were funnier, it’d be easier to forgive the rest of the film’s weaknesses: Its lack of emotion, the clumsy writing, the Farrelly-esque gags that occasionally veer into Jason Friedberg and Aaron Seltzer territory. Too often, The To Do List comes off as a bad parody of loss of virginity movies, instead of the smart satire it wants to be. The To Do List earns a lot of points for trying to be different, but not quite enough to make up for the deficit of good comedy.

Dustin is the founder and co-owner of Pajiba. You may email him here or follow him on Twitter.